Tributylvinyltin → HCID 69073653, compound

HRID 1785276Notes

Reaction equation

HRID 1785276 reaction equation
[F:1][C:2]1([F:32])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:31])([C:24]2[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=2)[C:8]([O:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[O:9])[CH2:3]1.[CH:33]([Sn](CCCC)(CCCC)CCCC)=[CH2:34]>O1CCOCC1>[F:1][C:2]1([F:32])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:31])([C:24]2[CH:29]=[CH:28][C:27]([CH:33]=[CH2:34])=[CH:26][CH:25]=2)[C:8]([O:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[O:9])[CH2:3]1

Participants

4

Reactant 2

HCID 81998TributylvinyltinHCID 69075853HCID 69075853, compound

Product 1

HCID 69073653HCID 69073653, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 125 mg of the t-butyl 4-((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-bromophenyl)ethanoyloxy)-tetrahydropyridine-1(2H)-carboxylate as obtained in Referential Example 52 in 4 ml of dioxane, 0.10 ml of vinyl tri-n-butyltin and 20 mg of tetrakistriphenylpalladium were added at room temperature, followed by 24 hours' heating under reflux at 110° C. in nitrogen atmosphere. Distilling the solvent off under reduced pressure, the resulting residue was diluted with ethyl acetate, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, the residue was purified on silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) to provide 90 mg of the title compound.

Workup

  1. temperature' heating
  2. distillationDistilling the solvent off under reduced pressure
  3. additionthe resulting residue was diluted with ethyl acetate
  4. washwashed successively with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationDistilling the solvent off under reduced pressure
  7. customthe residue was purified on silica gel column chromatography (eluent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-9a92957934934b2aabfa270d7030fb61
Source dataset
uspto-grants-2009_03
Patent number
US07504432B2

Reaction notes

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